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The dark web scene has been drawing the attention of law enforcement agencies and researchers alike. To date, most of the published works on the dark web are based on data gained by passive observation. To gain a more contextualized perspective, a study was conducted in which three vendors were selected on the "Dream Market" dark web marketplace, from whom subsequently several new psychoactive substances (NPS) were ordered. All transactions were documented from the initial drug deal solicitation to the final qualitative analysis of all received samples. From the selected vendors, a total of nine NPS samples was obtained, all of which were analyzed by NMR, HRMS, LC-UV, and two also by x-ray diffraction. According to our analyses, four of the five substances offered under already known NPS names contained a different NPS. The selected vendors therefore either did not know about their product, or deliberately deceived the buyers. Furthermore, two of three obtained samples of purportedly novel NPS were identified as already documented substances sold under a different name. However, the third characterized substance sold as "MPF-47700" was a novel, yet uncharacterized, NPS. Finally, we received a single undeclared substance, later identified as 5F-ADB. In addition to chemical analysis of the nine obtained NPS samples, the methodology used also yielded contextual information about the accessibility of NPS on the dark web, the associated purchase process, and the modus operandi of three NPS vendors. Direct participation in dark web marketplaces seems to provide additional layers of information useful for forensic studies.

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Kinetic and mechanistic aspects of an anodic oxidation of iodobenzene and its selected derivatives leading to the corresponding iodosyl compounds, were investigated in anhydrous acidic acetic acid environment using boron‐doped diamond electrode. The first electron removal leading to the formation of radical cation was identified as the rate determining step of the process. Oxidation potential values of the investigated compounds were rationalised by their solution phase ionisation energies (in conformation of the radical cations as products of the first electron removal), calculated by advanced DFT methods. Unexpectedly low oxidation potential of 2‐iodobenzoic acid and its functional derivatives compared to iodobenzene, 3‐iodo and 4‐iodobenzoic acids was explained by decreased electron density at iodine atom leading to planar 2‐iodobenzoic acid radical cation. This is connected with reordering of its frontier molecular orbitals compared to non‐planar neutral molecule.